Allen H. Whitehead III spent more than a decade building a successful career as a trusted financial adviser for one of Virginia's oldest and most-respected investment firms.

He was a deacon in his Williamsburg church, a benefactor and volunteer for several local charities - a pillar of the community who was quick with advice, whether financial, personal or spiritual.

An astute salesman and consummate gentleman, Whitehead amassed a vast book of clients at Richmond-based Davenport and Co. that included several prominent investors who relied on his steady hand to guide them through the tumultuous bull-and-bear market of the 2000s.

Many of those investors had such faith in him that they poured hundreds of thousands of dollars into a startup company Whitehead joined after leaving Davenport.

That's why those who knew and trusted him were so surprised - shocked, even - when Whitehead abandoned his family, declared bankruptcy, boarded his 45-foot yacht with the woman he left his wife for and sailed out of Virginia.

YORKTOWN NATIVE

Allen H. Whitehead III was born in 1966, the oldest of three children of Allen Whitehead Jr. and Patricia Whitehead of Yorktown. He graduated from York High School before setting off for Wake Forest University.

After college, he worked as an agent selling life insurance for Northwestern Mutual Life in Winston-Salem. In North Carolina, he met his future wife, Kristy Leigh Royall. They married in 1992.

The Whiteheads moved back to Hampton Roads shortly thereafter, and Allen began his career in Williamsburg as a financial adviser with Davenport, a conservative and highly regarded investment services firm founded in Richmond in 1863.

Success came quickly. In 1993, Allen was named Williamsburg Area Chamber of Commerce's 1994 Ambassador of the Year.

He spent the next decade building his client base at Davenport, and later at Legg Mason, that would grow to include many of Williamsburg's bold-faced names: attorneys, real estate developers and business executives.

In 2001, he and Legg Mason investment partner David Anderson brought their financial planning partnership back to Davenport.

Business was robust.

Two years after returning to Davenport, Whitehead, an avid sailor, built a 5,400-square-foot home in Ford's Colony in part to take advantage of its yachting center, friends said.

In 2004, the Whiteheads partnered with three other families to build a six-bedroom beach home in Duck, N.C., that has an assessed value of $941,300, according to Dare County property records.

"Allen was impressive," said Bob Gasink, a former friend and investor. "He was sharp and he did good work for his clients. Everyone he'd ever done anything for would tell you that he did a good job. People knew him and people liked him."

CHURCH AND COMMUNITY

What impressed people about Allen wasn't just his investment savvy. He wasn't the life of the party, rather the measured fellow who relished meaningful conversation. He preferred for his actions to shape his reputation.

His involvement in an assortment of charities and his leadership role at the Williamsburg Community Chapel gave investors confidence. His personality and civic involvement spoke of a man who was deeply invested in the community.

Whitehead was a key member of a team that raised money for the expansion of the church, which is attended by more than 2,200 congregants each Sunday. He led an effort to raise money for a translation of the Bible and made a trip to Africa to help distribute the books.

Former friends said it was a very important trip at the time for Allen, who described it to them as a "spiritual experience."

Whitehead was on the board of trustees for the Williamsburg Symphonia, involved with a Richmond-based organization that worked with inner-city children and mentored at least one inmate about to be released from prison, friends said.

"A lot of this was a facet of his faith," Anderson said.

The relationships Whitehead built in the community and at his church proved beneficial for his business. He counted among his investors several church members, including Perry Moore, an entrepreneur who owns and manages commercial real estate.

"He was an impressive young man, very polite, always looked perfectly dressed, had beautiful children. He was as smart as they come - just a wonderful guy," Moore said. "And I was very satisfied with the results he produced."

The more Whitehead produced for his clients, the more money he brought home. In 2007, Whitehead earned $530,575, public records show.

Sean Allburn, a fellow financial adviser at Davenport, called Whitehead "a respected colleague who did good work for his clients."

Above all, his friends and former co-workers said, Allen Whitehead was a family man who was committed to his wife and doted on his two daughters.

"I was in short a model father and husband, supporting every need of my family at the drop of a hat," Whitehead would later write in a court filing.

NEW OPPORTUNITIES

Toward the end of 2007, Whitehead was introduced to a group of entrepreneurs from Utah who were setting up a business to capitalize on cell phone company T-Mobile's plan to expand aggressively into East Coast markets. It was an introduction that would mark a major turning point in Whitehead's life - both personal and professional.

Headed up by a family of investors that included the husband-and-wife team of Christopher and Joyce Price, who was also known as Joyce Evans, and Trever Bybee, Joyce's son from a previous marriage, the startup incorporated in March 2008 and set up shop in Williamsburg's New Town.

The Mobile Team LLC planned to open dozens of retail stores and kiosks in the Mid-Atlantic region selling T-Mobile phones and service plans.

Whitehead, with the support of his family and some friends, left his job at Davenport in April 2008 to join the new company as its chief financial officer.

He poured much of his own fortune into the venture - about $900,000 up front, according to a filing in Williamsburg/James City County Circuit Court. Whitehead eventually built a 28 percent ownership stake in the firm.

"He felt he had a good business opportunity in front of him with great upside," said Scott Smith, a former friend. "He seemed very excited by it."

But for a man whose success was knotted with his conservative investment strategy, the high-risk, potentially high-reward world of venture capital seemed a stark departure.

Many of Whitehead's clients at Davenport were surprised by the move, which they say came abruptly and without notice.

"I was shocked," Moore said. "He was making good money, and he had a substantial client base. He just picked up and left."

Other investors and friends shared similar stories.

"I was disturbed," said Pressley "Pete" McCance, who invested with Whitehead for several years and grew to become friends with him. "I had no idea where he went, and I don't know that anyone else did, either. It was odd."